


You're into some freaky shit, huh?

by YlvaUllsdotter



Category: Supernatural
Genre: Anal Sex, Bondage, F/M, Pegging, Spanking, Sub!Dean, dom!reader
Language: English
Status: Completed
Published: 2017-10-30
Updated: 2017-10-30
Packaged: 2019-01-26 16:27:48
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 5,193
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12561460
Author URL: https://archiveofourown.org/users/YlvaUllsdotter/pseuds/YlvaUllsdotter
Summary: You let Dean borrow your laptop while his is getting scrubbed clean, and he finds your folder of porn bookmarks. It leads to more than you expected. One-shot. Rated for reasons. Pairing: Dean x Reader





	You're into some freaky shit, huh?

**Author's Note:**

> Original summary from this Tumblr post: post/162223570717/youre-into-some-freaky-shit-huh-for-the-title

You watched Dean pace with frequent glances toward your laptop for a while before closing down all your tabs and giving it a slight shove across the table.

"Here, use mine, before you wear a hole in the floor".

His frown turns into a smile as he cocks an eyebrow at you.

"Really?"

"Yeah, dude. I'm gonna go out for a while, you go ahead".

He plops his cute little ass down in the chair directly opposite you and pulls the laptop to him with a "thanks!", as you get up and head to the garage with the intention to drive into town for supplies.

Dean glances up as she disappears down the hall, appreciating the way her tight jeans hug her hips and backside, a small smirk playing on his lips, before turning back toward the borrowed laptop. He clicks open a browser window and focuses on his search.

A while later Dean is done with his research but Y/N is not back yet, so out of curiosity he decides to browse through her bookmarks. Clicking on the menu, he scans through a long list of bookmarks, none of them catching his eye, until he notices a folder at the top labeled simply "X". He raises an eyebrow and clicks to open the folder. As he scans through the bookmarks his eyes widen in surprise. They are all porn sites! That realization is quickly followed by another: these are not any kind of porn sites like what he usually looks at. Out of curiosity, he clicks on one at random. A [website](https://www.kink.com/channel/divinebitches) opens and he just stares for a moment. He knows he shouldn't, but he can't help himself, he clicks on one of the video links.

As the video loads, he looks around nervously, even though he knows he is alone. Sam is on a hunting trip with mom, and Y/N is still not back from her supply run. Still, his heart beats a little faster from fear of getting caught. Then the video is done loading. He jumps a little as the first sounds appear to echo in the cavernous library and pull his eyes back to the screen. Wide-eyed, he watches as a gorgeous woman dressed completely in tight black leather - super high heels and tightly laced corset, the whole nine yards - ties a guy up and proceeds to treat him like a piece of meat. He rubs suddenly sweaty palms on his jeans, surprised to feel his cock growing hard.

Sure, he's enjoyed the occasional light spanking, or having his nipples pinched, but this is on a whole other level, and he just didn't think he enjoyed this kind of thing, but apparently his cock has other ideas. Dean looks around again, before his eyes are drawn back to the video on the laptop screen. The guy seems to be enjoying the treatment, and Dean's eyes go a little unfocused as he imagines himself in the same sitation. He has to press the heel of his hand to his crotch to adjust himself, his now hard cock feeling uncomfortably constricted by the tight jeans. At the end of the video, he is surprised to see the participants smiling and completely at ease, talking to someone off camera about the experience. Curious, and more than a little turned on now, he clicks on another video. He is on his third, palming himself through his jeans and considering going to his room for some personal time, when he hears a door slam.

Dean panics, slamming the laptop shut and desperatly trying to think of dead puppies, ghoul guts, anything to get his hard cock to cooperate.

You flinch as the door to the garage slams behind you. With your hands full, you had to kick the door shut and apparently there was a draft. You roll your eyes at yourself as you head to the kitchen and unload the two bags of groceries, smiling fondly as you deposit the two pies in the fridge. You finish quickly and head out to the library, where you find Dean sitting with his legs crossed, reading a book. You squint at him, suspicious, because c'mon, Dean reading? Something's up.

"Hey. Got some pie, it's in the fridge".

Dean doesn't look up from his "reading", in fact he seems to sink further down into the armchair. He just nods and grunts. You sit down and pull your laptop across the table, looking at Dean curiously. You notice his face seems flushed, and you smirk, thinking you know what he's been up to while you were gone. Flipping open your laptop, you pause and tilt your head curiously. The video automatically resumes, and the sounds almost echo in the large space. You look over the top of the laptop at Dean, one eyebrow raised. His blushing face is buried in the book that he's definitely only using for cover.

"Dean".

He doesn't look up. You regard him quietly for a moment, pondering how to approach this. You suspect the reason why he's still sitting there, with his legs crossed, and a small smile plays over your lips. So.

"Dean, look at me".

Your tone is demanding, and sure enough after only a slight hesitation, he lifts his head out of the book and glances at you. He can't seem to look at you for long though, and his blush deepens. He doesn't seem to notice your smirk, and quickly lowers his head again. You get back up from where you just sat down and walk around the end of the table, glad you wore your heeled boots today as you notice his eyes flick to them when you stop in front of him.

"You've been a bad boy, Dean. Snooping around on my laptop. But I guess you liked what you found".

You didn't think he could blush any deeper. You were wrong. He flicks a glance up at you, then at your boots, before he looks back down again. He clears his throat and starts to speak but you don't let him.

"Snooping is a bad habit, Dean. Now what am I to do with you?"

You speak right over his attempt and notice him squirm a little in his seat. You get an idea.

"Stand up".

Your tone is still demanding, and Dean finds himself obeying, putting the book aside and standing, his hands crossed in front of him to try to hide his raging boner.

Dean is confused, and aroused, and curious where this is going. When Y/N steps in closer, he feels himself shiver in anticipation and he knows she notices. In her heels she is as tall as he is and when he looks up he is looking straight into her eyes and he can't break the contact, even if he wanted to, which he doesn't. He feels the pressure of her hand on him, just below his waist and sliding down until she is palming his erection through his jeans. Embarrassingly, he can't hold back a low moan at the contact.

You smirk at the sound Dean makes. Breaking the contact, you turn and walk down the hall toward the file room. At the doorway you turn and look over your shoulder, meeting Dean's eyes. You raise one eyebrow, then turn away and keep walking. You don't even have time to wonder if he's going to follow before you hear the sound of his boots behind you.

You wait by the file room door for him to enter, then close and lock the door behind him. Pulling the shelves aside, you enter the dungeon. You move the chair back toward the wall and point to the middle of the devil's trap.

"Stand here and strip".

Making yourself comfortable on the padded chair, you watch Dean intently. He hesitates for only a second before taking the last couple of steps to where you pointed and starts to pull his flannel shirt off, slowly and seductively. You cross your legs and lean back to enjoy the show.

Dean tosses the shirt to the side carelessly, then drops his hands to his belt, undoing it and pulling it off slowly. You can almost see his thought process in the expressions on his face and in his green eyes so you're not surprised when he drops the belt in front of him, looking straight at you. He pauses as if to see if you understood his meaning, but you make no move to either confirm or deny. A small frown of confusion passes over his face, before he goes on to unbutton his jeans. He toes off his boots and kicks them to the side before turning around to present his lovely backside as he shimmies out of the jeans. While he's still bent over, he removes his socks, tossing both pants and socks aside before standing back up and turning towards you. You can tell he's getting into the strip tease as he slides his hands under his t-shirt, caressing his skin and lifting the shirt up to expose more and more of himself. You watch as his hands move under the thin fabric that doesn't really hide anything, and can't hide a smirk as he plays with his nipples, rubbing and pinching them, before pulling the shirt off over his head and tossing it aside. He stills, standing there in just his boxer briefs, a cocky little smirk playing on his full lips.

You raise an eyebrow and gesture for him to continue. He blinks as he hesitates briefly, then slips the index finger of each hand into the waistband of the boxer briefs and runs them along his skin, as he turns around, once again presenting his cute little ass while he shimmies out of the underwear. When he turns back toward you, his hands are crossed over his crotch and his face is bright red.

Dean is hard as a rock, and completely embarrassed to be so in front of Y/N. He can actually feel the blush and knows his face, neck and shoulders must be a bright red. Which of course means every freckle is individually visible, which makes him even more embarrassed. He scans Y/N's face, trying to determine if she likes what she sees, or if she's just messing with him. He decides never to play poker with her, because he can't tell anything from her expression. Nervously, he waits for her next move.

You sit and just admire Dean's body. The blush is making each freckle stand out, the slight chill in the air has his nipples nicely puckered (or maybe he's just that aroused). You count to 60 in your head before gesturing for him to move his hands. When he just looks at you like he doesn't understand, you roll your eyes.

"Hands behind your back, Dean".

Again, you didn't think he could blush any deeper. Again, you were wrong. But he does as instructed, clasping his hands behind his back. You can't wait any longer so you stand and move in close to him, wrapping one hand around his shaft and drawing a ragged gasp from those plump lips. You want him completely on edge, so you start to stroke him firmly while your other hand finds his closest nipple and starts to pinch and twist. When he starts to thrust into your hand, you stop and step away, to the sound of his frustrated groan. He is breathing hard by now, his body flushed, muscles tense. You stand behind him where he can't see you and ponder what to do with him now that you have him here. Your eyes fall on his ass, and a slow grin spreads over your face. Reaching up, you grab one of the shackles hanging from the ceiling. When your hand grabs his wrist, he flinches at the contact. You raise his arm up and lock the shackle on his wrist, then quickly repeat with his other wrist. The shackles hang low, and Dean is a tall guy, so his arms hang loosely, elbows at eye height. Looking down you notice the eye bolt in the center of the devil's trap. After a quick search you find a pair of leg irons connected by a chain, and a padlock that fits, which you fasten to the eye bolt, then lock Dean's ankles in. This leaves him with some range of movement, but not enough to do much more than squirm.

You're only mildly surprised to find that his erection hasn't flagged at all during all this. Stepping in close to him, you wrap your fingers around said erection and stroke slowly while nipping at those luscious lips of his. You are completely turned on by how much he trusts you, letting you restrain him like this and you want him to know so you slip one hand into your own pants, sliding two fingers inside yourself, then bring those two fingers up to his lips.

"You're so hot like this, Dean. See how wet you made me".

He sucks your fingers into his mouth, licking your juices off. His eyes close and he hums in pleasure at tasting you. The sight of his plump lips sucking your fingers gets you even hotter. You move your hand from his shaft to stroke his hip and around to his ass, squeezing firmly, before stepping away from him.

"Don't go anywhere".

You hear a confused sound from him as you walk away. Outside the file room, you send a quick text to Sam. He replies immediately, confirming that he and Mary are going to be another day at least before heading back. With a satisfied grin you quickly retrieve what you need from your room. As you're closing the file room door behind you again, you hear Dean from behind the shelves.

Dean panics a little when Y/N left him restrained. He can't help yanking at the chains, even though he knows it's futile. Luckily he doesn't have time to go into full blown panic mode before she is back. He tries to analyze his feelings, and comes to the conclusion that he has always felt safe around Y/N right from the start. He trusts her, otherwise he wouldn't have let her restrain him. His memories of this dungeon aren't really that great after all. He feels himself relax when he hears Y/N return, then tense in anticipation. What was she going to do to him? He flinches at the thud when a black canvas duffel bag lands near his feet where he can see it. He starts to turn toward the sound of her boots on the cement floor, but decides not to. He locks his eyes on the bag instead, waiting.

You toss the duffel bag where you know Dean can see it and watch his reaction. He sways slightly as if he wanted to turn but stopped himself. You take two steps forward and lean toward him, placing your hands on his hips, and grin when he leans into your touch. You slide your hands from his hips, forward and up until you find his nipples, where you stop and play for a while until he is panting and unconsiously thrusting his hips, his head turned to the side eyes closed and biting down on his own arm to stifle his groans.

Stepping away, you chuckle quietly at his frustration, while you pull the duffel toward you. The sound of the zipper makes him flinch and without looking you know his eyes are locked on the bag, wondering what's in it. You turn away from him, pulling items out of the bag and lining them up on the seat of the chair. Only three items, but you are anticipating a strong reaction once Dean sees them. You push the duffel under the chair and stand, turning toward Dean, your body hiding the items from his sight for now. His eyes are locked on you as you pull your boots off, then start to unbutton your own jeans. He pulls a little on the restraints, then stills and just drinks in the sight of you as you shimmy out of your tight jeans, folding them neatly and setting them on top of the bag under the chair. You slip two fingers under the waistband of your simple white cotton panties and slip them off, thoroughly enjoying Dean's eyes riveted on you since you can see the appreciation in his expression, and in the way his hips thrust toward you unconsciously. You step aside so he can see the items on the chair.

Dean watches Y/N strip, well half way anyway, and he can almost feel the blood rushing to his already hard dick. It twitches in anticipation and he can't take his eyes off her. Then she steps aside to let him see what she left on the chair, and his eyes go wide. His heart beats hard in his chest and he can't tell if it's from fear or anticipation. Maybe both. His cock twitches and he licks his lips nervously. Does he trust Y/N that much? Yes. Yes he does. His eyes move from the items on the chair to look into Y/N's eyes and he nods slightly.

You study Dean's reaction closely, and you know, even before he looks at you and nods, that he's going to be ok with it. His eyes are dark from lust-blown pupils and he is breathing hard. You know those eyes follow your every move as you reach down and pick up the first item. The pop of the bottle cap is loud in the small space and out of the corner of your eye you see Dean flinch. You squeeze out a generous amount of lube before setting the bottle back down and moving behind Dean. One hand on his hip, you direct him with the pressure of your palm until he is in a better position, his feet as far from the bolt in the floor as the chain will allow. His hands have gripped the chain above him, and he's bending forward as much as he can in the restraints. You slide your hand from his hip, over his ass, and use the fingers of that hand to spread his cheeks apart. He is tense and flinches when he feels your slicked up fingers touch his puckered muscle. You lean into him and gently rub your fingers in circles around the tense muscle. Your other hand slides up to massage wider circles on his lower back while you place soft kisses along his shoulder blades.

"Relax"

Eventually he does, enough for you to slip one finger inside him. You quickly find his prostate and massage it, drawing a ragged gasp from him. When he's relaxed again, you slip in a second finger, continuing to massage his prostate. By the time you slip your third finger in, he is moaning low and thrusting his hips back onto your fingers. When you withdraw to collect the second item, you can't help but chuckle at his frustrated whimper. His green eyes follow you as you move into his line of sight, watching you pick up the second item. He watches you until he can't see you anymore, and you see him tense, then relax. When you touch him again, he thrusts his ass toward you, and you grin. The plug slips in easily, although you push and pull it a little, twisting it, to make sure it's seated securely and won't slip out. He hisses and moans at the sensations, rolling his hips when you take your hands away, as if savoring the feeling of the plug filling him.

Dean is just starting to feel overwhelmed, when Y/N pulls away and moves back in front of him. He watches her pick up the plug, his eyes following her until she moves out of his line of sight. The thought of the plug invading him makes him tense, then the memory of how her fingers felt makes him relax. When he feels her hand on him, he licks his lips and is only vaguely aware of thrusting his ass toward her. He breathes hard as the plug slips inside him, his cock twitching. He expects to be hard as a rock and leaking precum, but realizes he is actually mostly soft. For a moment his brain short-circuits from confusion, as he always associated the level of pleasure he had felt with being hard, and didn't know that you could feel that kind of pleasure just from what Y/N had done to him. He feels confused, but all thoughts leave his brain when he feels Y/N pushing and pulling and twisting the plug inside him. He has to bite down on his bottom lip to stop himself from begging for more.

You stand there for a moment and just drink in how ridiculously hot Dean looks, chained up and filled up, flushed, breathing hard, his plump bottom lip caught in his teeth. You lean down and pick up the belt he discarded earlier. You grab his face with one hand and hold the belt up with the other, making sure he focuses on you before you start talking.

"Now, Dean, you were a bad boy, and I can't have that. Snooping is a bad habit, and bad habits have to be corrected. You're probably not going to enjoy this, but punishments aren't supposed to be enjoyable after all. If you can take your punishment like a good boy, you'll be rewarded after".

Dean's eyes flicker between your face and the belt, a glimmer of fear showing for a moment before he nods once without saying anything. You pat his cheek gently, and can't resist leaning in for a kiss which begins slow and soft, but quickly becomes hard and demanding. His luscious lips give easily under the press of yours. You break off the kiss abruptly and move behind him.

"Twenty strokes. Count them. If you miss one, I'll start over".

Without any more warning, you pull back and whip the belt forward with a flick of the wrist. It lands on his ass with a satisfying smack and you let it fall while you wait.

Dean barely has time to register what Y/N said before the pain blossoms on his ass where the belt struck. His whole body tenses as the pain registers but finally he manages to push out a muffled "one" through his clenched teeth. The next stroke lands immediately after that, drawing a whimper from him. After the fifth stroke, he tries to draw out the time it takes him to count out loud, but Y/N calls his bluff right away. By the tenth stroke, he is just crying out the number as quickly as he can. By the fourteenth, his tears are making wet spots on the concrete floor. Even as he cries out "twenty", he doesn't register that that is the last one, not until he realizes no more blows are coming. His hands are gripping the chain above him so tightly it hurts and his ass and thighs feel like they're on fire. He flinches when he feels her hand on him.

You are breathing hard after the twentieth stroke, you didn't hold back at all, knowing Dean could take it. Letting the belt drop to the floor you step in close to him and gently caress his welted ass. You smirk as he flinches, but don't stop your hands softly stroking his ass and upper thighs. He's going to have trouble sitting for a few days, a thought that makes you grin with satisfaction. You move in front of him and put two fingers under his chin, lifting his head up so you can place a tender kiss on those lovely lips. You spend a little while gently exploring his lips and mouth until you feel him responding. Running your fingers through his damp hair, you smile at him.

"Good boy. I think you've learned your lesson, and earned your reward".

The look in his eyes is one of gratitude and anticipation, like a puppy being promised a treat. Somehow you're not surprised, you sort of always knew Dean was a sub deep down. Or maybe not so deep down.

Moving away from him, you can feel his eyes on you as you pick up the last item on the chair and start to buckle the straps on around your hips. Out of the corner of your eye you can see Dean moving slightly, rolling his hips tentatively and licking his lips. The strap-on is purple, because you like purple, and it's about the same size as Dean's own cock, which is twitching in anticipation. You hiss a little from pleasure as you slip the other end of it inside your dripping wet pussy. Dean's submission, and trust in you, has you more turned on that you've been in...ever.

Straps buckled, you wrap your fingers around your silicone cock and stroke it slowly while stepping closer to Dean. You stop when the tip of your cock is almost touching Dean's lips and watch how his tongue flicks out to lick his lips. His eyes are locked on the cock that is nearly touching him, your fingers wrapped around the base of it.

"Go ahead, lick it. I know you want to".

His adam's apple bobs as he swallows hard, before sticking his tongue out and hesitantly licking the head of your cock. His mouth is open just enough that it slips easily between his lips when you thrust your hips forward. His eyes widen in surprise, and flick up to glance at your face, only to meet your wicked grin. Taking half a step forward, you rock your hips, watching your purple dick slide between Dean's plump lips, lips that were surely made to be wrapped around a cock. Your fingers card through his hair before you tighten your grip, holding his head still for you to fuck his mouth. He gags a little as the cock hits the back of his throat, but he doesn't try to pull away. The sight of his lips on your cock coupled with the stimulation of your g-spot and clit almost has you coming. You pull out of Dean's mouth, watching him as you reach for the bottle of lube. You squeeze out a generous amount before wrapping your hand around your cock and slicking it up. Dean's eyes are riveted on you, watching your actions with his lips slightly parted, breathing heavily. You can see his cock, now hard again, twitching, drops of precum forming and dribbling down his hard shaft.

Without a word, you walk behind him and stroke his welted skin with your free hand. Your fingers find their way to the plug still seated in his ass and you carefully, and slowly, pull it free. You toss it seemingly carelessly on the floor, making sure it lands where Dean can see it clearly. With your lube-slick hand you circle two fingers around his hole before again grabbing your cock and guiding it in. Dean's hips twitch when he feels the slick head of your strap-on press against his hole, as if he wants to pull away, but only for a moment. He stills, and you push slowly but implacably. With your free hand, you grab his hip as your cock pushes steadily into him. The noises he is making are making you want to just slam into him in one hard thrust and fuck him senseless, but you grind your teeth and take it slow.

Dean is only moderately surprised when he feels his cock grow hard watching Y/N stroke her strap-on cock. When she pushes into his mouth he lets his brain shut down and just holds on. Feeling the strap-on push inside him, he grips the chains above him tightly and pants hard. Both his hole and the dildo are well lubed, so it doesn't exactly hurt but it's a weird and uncomfortable feeling all the same. Until she hits his prostate. His mind blanks, all thoughts shut off and his whole universe is compressed to this one point where their bodies are joined and the sensation of her cock sliding against his prostate and it feels so fucking good he is going to explode and he wants it to last forever.

You know you've hit the spot when you hear Dean groan low and feel his hips thrust back toward you. Grabbing both of his hips to control the pace, you pull out slightly, then push in, knowing your cock is rubbing his prostate each time. Holding him still, you set a slow and regular pace, thrusting in and out only an inch at a time. Within seconds, Dean is whimpering, his grip on the chains above him so tight his knuckles are white. You reach a hand around him to wrap around his cock and stroke it in time with your thrusts.

"Tell me, Dean. Tell me what you want".

You coax him, keeping the same pace, slow and excruciating, for both of you, as he writhes and squirms under you, trying to control the pace, pick it up, get more friction. You chuckle, and maintain control easily. Finally, he speaks, his voice cracked and ragged, husky with desperate need.

"Please, Y/N, please..."

"Please what, Dean? Tell me what you want".

"...fuck me, Y/N...!"

You laugh softly as you grip his hips tighter, pulling him back onto your cock, thrusting hard into him and picking up the pace. Your own breath hitches as you get closer to climaxing, but you clench your teeth and focus on him. One hand slides from his hip up his back and comes to rest between his shoulder blades. The other hand soon follows and both of them slide around his front, pausing at his nipples to pinch and twist, drawing a groan from him. You settle both hands on either shoulder, using the grip for leverage as you fuck him hard. You lean in and growl into his ear.

"Come for me, Dean".

Dean makes an absolutely delicious noise somewhere between a moan and a sob, his body tenses and shudders. Crying out your name he comes hard, and you hold on tight, hugging him from behind. His sounds easily push you over the edge and with a last couple of thrusts, you bury your cock deep inside him as you shudder with your own orgasm.

Later, you're sitting at the edge of Dean's bed, having just tucked him in for a nap. He looks up at you with an expression of wonder and awe. You laugh softly.

"What, Dean?"

"What? Oh. Sorry. I just... I never knew... I just, never knew".

"I know. It's ok. Don't overthink it. It is what it is".

Dean nods, as if your cryptic words make perfect sense. His soft lips stretch into his trademark shit-eating-grin.

"I should've snooped on your laptop months ago".


End file.
